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Aliskiren

AlkaPlorer ID: AK084768

Synonym: None

IUPAC Name: (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide

Structure

SMILES: COCCCOC1=CC(C[C@@H](C[C@H](N)[C@@H](O)C[C@H](C(=O)NCC(C)(C)C(N)=O)C(C)C)C(C)C)=CC=C1OC

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InChI: InChI=1S/C30H53N3O6/c1-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36/h10-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35)/t22-,23-,24-,25-/m0/s1

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InChIKey: UXOWGYHJODZGMF-QORCZRPOSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain

Properties Information

Molecule Weight: 551.7690000000003

TPSA？: 146.13

MolLogP？: 3.2935000000000043

Number of H-Donors: 4

Number of H-Acceptors: 7

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Cathepsin D IC50 100000.0 nM 10.1016/j.bmcl.2009.05.128
Callithrix jacchus Callithrix jacchus F 16.0 % 10.1021/jm901885s
Callithrix jacchus Renin Activity nan None 10.1016/j.bmcl.2009.05.128
Canis lupus familiaris Canis familiaris F 32.0 % 10.1021/jm901885s
Canis lupus familiaris MDCK Papp 1.0 ucm/s 10.1039/C1MD00093D
Canis lupus familiaris MDCK Ratio 0.7 None 10.1016/j.bmcl.2010.10.140
Canis lupus familiaris MDCK Ratio 1.5 None 10.1016/j.bmcl.2010.10.140
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A2a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2b adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2c adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-1 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-2 adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Bradykinin B2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cannabinoid CB1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin A receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cholecystokinin B receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cytochrome P450 1A2 Inhibition -12.4 % None
Homo sapiens Cytochrome P450 1A2 Inhibition -6.4 % None
Homo sapiens Cytochrome P450 1A2 Inhibition -5.8 % None
Homo sapiens Cytochrome P450 1A2 Inhibition 2.5 % None
Homo sapiens Cytochrome P450 1A2 Inhibition 5.0 % None
Homo sapiens Cytochrome P450 1A2 Inhibition 6.0 % None
Homo sapiens Cytochrome P450 1A2 Inhibition 15.2 % None
Homo sapiens Cytochrome P450 2A6 Inhibition -2.1 % None
Homo sapiens Cytochrome P450 2A6 Inhibition 2.6 % None
Homo sapiens Cytochrome P450 2A6 Inhibition 10.5 % None
Homo sapiens Cytochrome P450 2C19 Inhibition -15.4 % None
Homo sapiens Cytochrome P450 2C19 Inhibition -1.9 % None
Homo sapiens Cytochrome P450 2C19 Inhibition -1.5 % None
Homo sapiens Cytochrome P450 2C19 Inhibition 3.0 % None
Homo sapiens Cytochrome P450 2C19 Inhibition 5.1 % None
Homo sapiens Cytochrome P450 2C19 Inhibition 9.6 % None
Homo sapiens Cytochrome P450 2C19 Inhibition 42.5 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 0.9 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 1.3 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 4.5 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 13.1 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 14.9 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 15.8 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 23.0 % None
Homo sapiens Cytochrome P450 2C9 Inhibition 32.1 % None
Homo sapiens Cytochrome P450 2D6 Inhibition 32.9 % None
Homo sapiens Cytochrome P450 2D6 Inhibition 37.0 % None
Homo sapiens Cytochrome P450 2E1 Inhibition -12.8 % None
Homo sapiens Cytochrome P450 3A4 Inhibition 11.0 % None
Homo sapiens Cytochrome P450 3A4/3A5 Inhibition -16.6 % None
Homo sapiens Delta opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Endothelin receptor ET-A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Equilibrative nucleoside transporter 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Ghrelin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Glucocorticoid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -7.46 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 6.65 % 10.6019/CHEMBL4808148
Homo sapiens Homo sapiens DILI_Concern nan None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens DILI_severity_class 0.0 None 10.1016/j.drudis.2016.02.015
Homo sapiens Homo sapiens F 2.5 % 10.1016/j.bmcl.2015.02.003
Homo sapiens Homo sapiens F 2.6 % 10.1016/j.bmc.2018.04.051
Homo sapiens Homo sapiens F 3.0 % 10.1016/j.bmc.2017.05.032
Homo sapiens Homo sapiens F 3.0 % 10.1039/C1MD00093D
Homo sapiens Homo sapiens F 4.0 % 10.1021/jm900022f
Homo sapiens Kappa opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Melanocortin receptor 3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Motilin receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M3 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuronal acetylcholine receptor protein alpha-4 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Neuropeptide Y receptor type 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4D AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Pregnane X receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Renin IC50 0.4 nM 10.1021/ml200137x
Homo sapiens Renin IC50 0.5 nM 10.1016/j.bmcl.2009.04.140
Homo sapiens Renin IC50 0.53 nM 10.1016/j.bmcl.2009.11.066
Homo sapiens Renin IC50 0.53 nM 10.1021/ml200137x
Homo sapiens Renin IC50 0.6 nM 10.1016/j.bmc.2017.05.032
Homo sapiens Renin IC50 0.6 nM 10.1016/j.bmcl.2009.04.140
Homo sapiens Renin IC50 0.6 nM 10.1016/j.bmcl.2009.05.128
Homo sapiens Renin IC50 0.6 nM 10.1016/j.bmcl.2015.02.003
Homo sapiens Renin IC50 0.6 nM 10.1016/j.ejmech.2011.03.035
Homo sapiens Renin IC50 0.6 nM 10.1021/acsmedchemlett.2c00280
Homo sapiens Renin IC50 0.6 nM 10.1021/jm300180r
Homo sapiens Renin IC50 0.6 nM 10.1021/jm900022f
Homo sapiens Renin IC50 0.6 nM 10.1021/jm901885s
Homo sapiens Renin IC50 0.65 nM 10.1016/j.bmcl.2009.11.066
Homo sapiens Renin IC50 0.65 nM 10.1021/ml200137x
Homo sapiens Renin IC50 0.7 nM 10.1021/acs.jmedchem.2c00834
Homo sapiens Renin IC50 0.7 nM 10.1021/acsmedchemlett.2c00280
Homo sapiens Renin IC50 0.84 nM 10.1016/j.bmc.2018.04.051
Homo sapiens Renin IC50 2.21 nM 10.1016/j.bmc.2011.05.059
Homo sapiens Renin IC50 2.3 nM 10.1016/j.ejmech.2015.08.060
Homo sapiens Renin IC50 2.5 nM 10.1021/acs.jmedchem.2c00834
Homo sapiens Renin IC50 2.5 nM 10.1021/acsmedchemlett.2c00280
Homo sapiens Renin IC50 3.0 nM 10.1016/j.bmc.2017.05.032
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 10000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2a (5-HT2a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2c (5-HT2c) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 3a (5-HT3a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Type-1 angiotensin II receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V1a receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vasopressin V2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Human immunodeficiency virus 1 Protease Ki 76.5 nM 10.1021/jm300180r
Macaca fascicularis Cynomolgus monkey Activity 30.0 mmHg 10.1021/acs.jmedchem.2c00834
Macaca fascicularis Cynomolgus monkey Activity nan None 10.1021/acs.jmedchem.2c00834
Macaca fascicularis Cynomolgus monkey AOC 322.0 mmHg.hr 10.1021/acs.jmedchem.2c00834
Macaca fascicularis Cynomolgus monkey AOC 328.0 mmHg.hr 10.1021/acs.jmedchem.2c00834
Macaca fascicularis Cynomolgus monkey AUC 25.9 ng.hr.mL-1 10.1016/j.bmc.2018.04.051
Macaca fascicularis Cynomolgus monkey AUC 154.0 ng.hr.mL-1 10.1016/j.bmcl.2009.11.066
Macaca fascicularis Cynomolgus monkey AUC 501.0 ng.hr.mL-1 10.1016/j.bmc.2018.04.051
Macaca fascicularis Cynomolgus monkey CL 2.5 mL.min-1.kg-1 10.1016/j.bmcl.2009.11.066
Macaca fascicularis Cynomolgus monkey CL 3.367 mL.min-1.kg-1 10.1016/j.bmc.2018.04.051
Macaca fascicularis Cynomolgus monkey Cmax 6.343 nM 10.1016/j.bmc.2018.04.051
Macaca fascicularis Cynomolgus monkey Cmax 53.46 nM 10.1016/j.bmcl.2009.11.066
Macaca fascicularis Cynomolgus monkey F 0.6 % 10.1016/j.bmc.2018.04.051
Macaca fascicularis Cynomolgus monkey F 1.4 % 10.1016/j.bmcl.2009.11.066
Macaca fascicularis Cynomolgus monkey Inhibition nan % 10.1016/j.bmc.2018.04.051
Macaca fascicularis Cynomolgus monkey T1/2 9.8 hr 10.1016/j.bmcl.2009.11.066
Macaca fascicularis Cynomolgus monkey Tmax 1.3 hr 10.1016/j.bmcl.2009.11.066
Macaca fascicularis Cynomolgus monkey Tmax 3.33 hr 10.1016/j.bmc.2018.04.051
Macaca fascicularis Cynomolgus monkey Vdss 1.5 L.kg-1 10.1016/j.bmcl.2009.11.066
Macaca mulatta Renin IC50 1.2 nM 10.1016/j.bmc.2018.04.051
Mus musculus Mus musculus Activity nan None 10.1016/j.ejmech.2015.08.060
Mus musculus Mus musculus Activity nan None 10.1021/acs.jmedchem.2c00834
Mus musculus Renin IC50 4.5 nM 10.1021/jm901885s
Oryctolagus cuniculus Renin IC50 11.0 nM 10.1021/jm901885s
Rattus norvegicus Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Glutamate (NMDA) receptor subunit zeta 1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus Rattus norvegicus Activity 43.0 mmHg 10.1016/j.bmcl.2015.02.003
Rattus norvegicus Rattus norvegicus Activity nan None 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Rattus norvegicus AUC 21.0 ng.hr.mL-1 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Rattus norvegicus CL 55.0 mL.min-1.kg-1 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Rattus norvegicus Cmax 7.249 nM 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Rattus norvegicus F 0.1 % 10.1039/C1MD00093D
Rattus norvegicus Rattus norvegicus F 1.2 % 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Rattus norvegicus F 2.4 % 10.1016/j.bmcl.2009.04.140
Rattus norvegicus Rattus norvegicus F 2.4 % 10.1021/jm901885s
Rattus norvegicus Rattus norvegicus Fabs 0.5 % 10.1039/C1MD00093D
Rattus norvegicus Rattus norvegicus T1/2 13.5 hr 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Rattus norvegicus Tmax 0.1 hr 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Rattus norvegicus Vdss 62.0 L.kg-1 10.1016/j.bmcl.2009.11.066
Rattus norvegicus Renin IC50 80.0 nM 10.1021/jm901885s
Rattus norvegicus Renin IC50 88.0 nM 10.1016/j.bmc.2018.04.051
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 10.09 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.2097 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.0 % 10.6019/CHEMBL4495565
None ADMET AUC 266.0 ng.hr.mL-1 None
None ADMET AUC 356.0 ng.hr.mL-1 None
None ADMET AUC 530.0 ng.hr.mL-1 None
None ADMET AUC 627.0 ng.hr.mL-1 None
None ADMET AUC 868.0 ng.hr.mL-1 None
None ADMET AUC 1480.0 ng.hr.mL-1 None
None ADMET AUC 1620.0 ng.hr.mL-1 None
None ADMET AUC 3240.0 ng.hr.mL-1 None
None ADMET AUC 3520.0 ng.hr.mL-1 None
None ADMET AUC 23806.0 ng.hr.mL-1 None
None ADMET CL/F 222.0 L.h-1 None
None ADMET CL/F 254.0 L.h-1 None
None ADMET CL/F 294.0 L.h-1 None
None ADMET CL/F 321.0 L.h-1 None
None ADMET Cmax 47.12 nM None
None ADMET Cmax 130.49 nM None
None ADMET Cmax 366.09 nM None
None ADMET Cmax 761.19 nM None
None ADMET Compound recovery 0.4 % None
None ADMET Compound recovery 2.0 % None
None ADMET Compound recovery 2.3 % None
None ADMET Compound recovery 3.0 % None
None ADMET Compound recovery 36.0 % None
None ADMET Compound recovery 40.0 % None
None ADMET Compound recovery 43.0 % None
None ADMET Compound recovery 60.4 % None
None ADMET Compound recovery 61.8 % None
None ADMET Compound recovery 64.3 % None
None ADMET Compound recovery 77.5 % None
None ADMET Compound recovery 78.0 % None
None ADMET Compound recovery 79.8 % None
None ADMET Compound recovery 80.0 % None
None ADMET F 1.8 % 10.1021/acs.jmedchem.2c00834
None ADMET F 2.4 % 10.1021/acs.jmedchem.2c00834
None ADMET F 2.5 % 10.1016/j.bmc.2020.115466
None ADMET F 2.6 % 10.1016/j.bmc.2016.09.030
None ADMET F 2.6 % 10.1021/acs.jmedchem.2c00834
None ADMET F 2.6 % 10.1021/acsmedchemlett.2c00280
None ADMET F 3.0 % None
None ADMET PPB 49.5 % 10.1016/j.bmc.2020.115466
None ADMET T1/2 24.0 hr 10.1016/j.bmc.2020.115466
None ADMET T1/2 34.0 hr None
None ADMET T1/2 37.0 hr None
None ADMET T1/2 41.0 hr None
None ADMET T1/2 54.0 hr None
None ADMET Tmax 1.0 hr None
None ADMET Tmax 2.0 hr None
None ADMET Tmax 2.5 hr None
None ADMET Tmax 3.0 hr None
None Hepatotoxicity HepSE_bilirubinemia 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholecystitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cholelithiasis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_cirrhosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_Combined Scores 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_elevated liver function tests 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic failure 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatic necrosis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatitis 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_hepatomegaly 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_jaundice 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver disease 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver fatty 0.0 None 10.1371/journal.pcbi.1002310
None Hepatotoxicity HepSE_liver function tests abnormal 0.0 None 10.1371/journal.pcbi.1002310
None NON-PROTEIN TARGET Activity nan None 10.1021/acsmedchemlett.6b00251
None NON-PROTEIN TARGET Potency 0.9 nM None
None NON-PROTEIN TARGET Potency 8407.1 nM None
None NON-PROTEIN TARGET Potency 11875.4 nM None
None NON-PROTEIN TARGET Potency 16774.4 nM None
None No relevant target LogP 2.45 None 10.1016/j.bmc.2020.115466
None No relevant target pKa 9.8 None 10.1016/j.bmc.2017.05.032
None No relevant target Solubility 350000.0 ug.mL-1 10.1016/j.bmc.2020.115466
None Unchecked IC50 100000.0 nM 10.1016/j.bmcl.2009.05.128

Metabolism Information